Mountain Lion from Scratch—Not as difficult as I thought it would be

Two weeks ago I gave in to the temptation to install Mountain Lion on my aging iMac. Immediately, I began to see evidence that entropy was catching up to me after years of upgrades. The first sign was when my password safe application crashed every time I launched it. Their support team started asking me to try this and that and send them logs, but things weren’t looking promising. I then tried to open iPhoto and that application crashed. And it continued to crash. Even if I uninstalled it, reinstalled it, moved the library, held down five magic keys while clicking my heels together on startup, I could not get iPhoto to launch.

That did it for me: if Apple’s own application is crashing, it’s time for a clean wipe and install. Here are some notes on my efforts and progress. I hope my brief adventure can help others to also have a smooth installation experience. Read on for the gory details…

Stuff I Learned

To cut to the chase, here is a short list of the salient elements of my efforts:

  • The App Store is incredibly helpful when doing a full wipe
  • Carbon Copy Cloner rocks!
  • There’s nothing like having a bootable copy of your old system nearby
  • No matter how carefully you try to migrate everything, you will forget some of the smaller stuff
  • There’s no way to remember how you did all of the little adjustments and tweaks over the years
  • Older printers are annoying
  • But it sure feels … soothing … to have a virgin installation of the latest and greatest OS on a clean hard drive.

Staying with last year’s version is never an option!

Every time a new version of OS X comes out, I go through the same process:

I spend a few days reading up on it, looking for the one killer feature I absolutely must have that will make the decision for me. For example, with Leopard, the feature that made up my mind was Time Machine. I haven’t seen such a compelling feature since Leopard—that version seems to have been the one where they got everything right.

I am then left looking at the various bells and whistles that the new version offers, wondering which one would make a difference in my life. Then I fret over the twin specter of incompatibility and lackadaisical application support: What’s going to break? How long before some little software company gets around to patching their apps?

I remember how Leopard broke hi-resolution printing to my LaserJet 1320 printer. I called AppleCare about it on multiple occasions and never got anywhere. HP didn’t seem to care either. Magically, the hi-res printing problem healed itself with Snow Leopard.

Do I really want to risk all of my data, gamble with broken applications, invite frustration, and pay for the privilege? After endless fretting and deep thought, I always give in, and within a week of any release I throw caution to the wind and install that sucker on my machine. Time Machine is always there to bail me out!

The Mountain Lion Installer

Mountain Lion does not come on a DVD; you install it from the App Store. But there is no App Store when you are wiping your machine clean.

I purchased an 8GB USB drive at Stables for six bucks and followed these excellent instructions to create a Mountain Lion USB-drive installer.

Getting Ready

If one is going to obliterate every trace of data from the computer hard drive, it is absolutely essential that everything important be somewhere else.

Here was my checklist:

  • Create a full bootable backup of my hard drive, so I can run the old machine to get at weird settings and such.
  • Create a full nonbootable backup elsewhere (e.g. a disk image). This can be mounted read-only so that you can’t mess it up when retrieving data.
  • Go through everything in the Applications folder and see what I really use (no need to reinstall some lame video stabilizer app I tried three years ago since I don’t mess with video).
  • Dig up the license keys for everything I need.
  • Identify the data for everything I need.
  • Figure out all of the weird tweaks I need (Folder Actions anyone?)

In the end, I put together a spreadsheet in Numbers:

It goes without saying that the spreadsheet needs to be available on a different machine. I took advantage of my slightly clunky Mountain Lion first attempt to use the iCloud storage for Numbers, so I could access the same document on my iPad. Slick!

In this spreadsheet I included each application name, the license key if I needed it, information about data the app uses, and any weirdness about the app.

Some apps were simple, such as iTunes: it’s an Apple app and I just need to make sure I have my iTunes library.

Other apps were head scratchers; for example, I use a neat little plugin called PTLens to remove lens distortion in Aperture. There is no license key for this app: you get a registration email with a link that is valid for one week only that lets you download a key file. Fortunately for me, the link was actually valid for many months after I purchased my key.

Another special case was my Windows virtual machine. I use VirtualBox to run Windows XP on my Mac, but the virtual machine file is excluded from my Time Machine backups because it changes every single time I run it, and I didn’t want a multi-gig file being replaced in Time Machine several times a week. I had to make sure that I would have that file intact, knowing that it wouldn’t be available from Time Machine.

Faded Memories of Tweaks

I went through all of the special adjustments I have made over the years to see what I would need to grab.

For example, I have a folder on my desktop called “Export” where I export photos from Aperture. I like to have the file timestamp match the EXIF date within the file, so I had done … something magical but long forgotten … that would wake up after Aperture finished exporting and it would change the file timestamps. A bit of forensic analysis was in order.

As it turned out, I had written a tiny Automator action that called a small shell script that ran the jhead utility to extract the EXIF date and adjust the file date. That meant I needed to back up the Automator action as well as the jhead utility.

Another tweak I have used over the years is my AppleScript solution for queueing ScanSnap scanned PDF documents for OCR processing. Fortunately, the Abbyy FineReader folks have finally fixed their ScanSnap app to support queueing without my script. That is one headache I don’t have to worry about anymore.

Backup One and Backup Two

I used the venerable Carbon Copy Cloner tool to make both my bootable backup and my non-bootable backup. The bootable backup is on an external hard drive I had sitting around; the non-bootable backup is in a disk image on another external hard drive.

Carbon Copy Cloner is very nice about warning you about issues that may arise in your backup. For example, it told me that my external hard drive had an undesirable partitioning scheme and recommended that I use Disk Utility to fix things up.

Here are the recommended settings:

Even after repartitioning and reformatting the drive, CCC warned me about a missing recovery partition and kindly created one for me. I was using Carbon Copy Cloner in the free trial period,, but I was so happy with its performance in this exercise that I will likely end up buying a copy.

The second backup was to a non-bootable sparse disk image that CCC made for me. It is by definition not bootable: you cannot boot from a disk image file.

Installing Mountain Lion

The actual installation is a breeze, and there are doubtless many sites that cover how to install Mountain Lion.

My installation process was as follows:

  • Insert USB Key with Mountain Lion and restart machine
  • Hold down the Option key as soon as the machine powers on. This will bring you to the boot selection screen.
  • Use the arrow keys to select the USB drive (gold) that has your installer.
  • Use Disk Utility to reformat the hard drive
  • Install Mountain Lion

As part of the process, you are prompted for your Apple ID to log in to iCloud and the App Store.

Installation Part I: The App Store

At this point, I want to draw attention to how convenient the App Store is during the reinstallation process.

Think about how old-style apps work: you buy them, you download them, install them, type in your license key, lose the key, occasionally look for updates, and eventually you end up searching for that key when you need to reinstall on a new machine. Fortunately, most reputable sellers will send it to you if you ask nicely.

With the Apple Store, you just log in with your Apple ID and click the Purchases tab. All of your apps are there, one click away from installation. The first thing I did after booting Mountain Lion on the vanilla drive was to enter my Apple ID and click “Install” on all of my App Store purchases.

I went to dinner and came back to find that the installer stops installing when the machine goes to sleep. I then quickly installed my favorite keep-awake app, Caffeine, from the App Store, and kicked off the “install everything” process again. A half hour later my virgin Mountain Lion installation had Pages, Numbers, iPhoto, and Aperture, among several other apps, ready to go. It was the easiest installation I have ever done. In short, from now on it is worth it to me to skip my upgrade discount on out-of-store purchases and buy it in the App Store.

Installation Part II: Everything Else

As convenient as the App Store is, a large number of my applications are either not available there or I own the latest version already and don’t want to repurchase it just to have it come from the App Store.

I downloaded the latest and greatest versions of apps such as Silver Efex Pro and TextMate and installed them, grumbling at app designers who don’t let me paste in a license key but force me to type it into little boxes.

I downloaded the Microsoft Office 11 installer and installed the full Office suite. I had been concerned about whether or not my key code would reactivate correctly, or if I had “used” my one and only activation when I installed it last year on Lion. MS Office activated quite nicely with my existing key and I was good to go.

Note that even if the key had not worked, it wouldn’t have been a disaster: Microsoft is pretty good at doing phone activations as long as you give a plausible explanation (e.g. “wipe and install”).

Bringing On the Data

Note: Before I did anything else, I selected the dmg file for my backup image, I hit Command-I to bring up its Get Info window and I ticked the Locked checkbox. This made the image file read-only. I can copy stuff from it, but I won’t accidentally delete or change any files on the backup.

Copying over data from backups is very easy for the major Apple products: just copy the libraries over.

For Aperture and iPhoto, copy the libraries from your backup to your Pictures folder. Then double-click on the library. This will launch the application with that library.

For iTunes, copy the library from your backup to your Music folder before you first launch iTunes. Then launch iTunes the normal way; it will detect the library automatically.

I made sure to copy everything from my Documents backup into my new Documents folder.

This is a good time to mention my favorite tool for slinging files around: ForkLift.

This is a powerhouse of a file management app that lets you open any kind of storage location in each of its two panes and lets you drag/drop and synchronize between them. You could have two remote servers open or two local folders open, or even your local hard drive and the backup disk image.

I used ForkLift to copy all of the files I needed from my data backup to the new machine.

Setting up my Printer

In most geek’s homes, it is quite possible that the oldest piece of hardware is the printer. This is because they often work well for many years, and if you spent a large sum of money on a good laser printer, you want to continue to use it until it dies.

In one annoying bit of “Apple Knows Best” design, OS X does not come pre-loaded with all of the available printer drivers, but you are not allowed to manually pick uninstalled drivers.

I have a nice aging HP LaserJet 1320 stashed away in a cabinet in my family room. It is hooked up to my network via a Netgear Print Server, and this configuration has worked fine for many years. The trick is to know how to set up a Unix network printer (often referred to as “lpr” printer) on all of your machines. You need the IP address and queue name for the target printer. And you need the printer driver to already be installed on your machine.

I entered all of the correct information in the “Add Printer” dialog, but I could not find LaserJet 1320 in the dropdown list.

As it turns out, HP tells you that OS X comes with all of the drivers, but Apple chose to only install the driver if the Mac actually sees the printer locally.

Yes, I had to lug my printer down to the basement next to my iMac for one single hot date where they would meet face to face and connect over USB. Once I did this, Mountain Lion detected the unfamiliar printer and asked me for permission to download the driver. I was then able to lug the printer back upstairs and put it back in its cubby and configure it as a network printer.

What exactly do people do when the printer is at work over a VPN or something like that?

Other Annoyances

Small things continually crop up, but nothing very serious. For example, I had several droplets configured for A Better Finder Rename and A Better Finder Attributes, but when I upgraded the software the droplets don’t work anymore. I suppose that if I had installed the old versions first and upgraded this wouldn’t have happened. It’s no great loss, since they are named clearly.

Network drives continue to be less than perfect. I don’t understand how Windows file shares seem to work so painlessly on the ancient Window XP platform, but OS X has always made such a mystery of connecting to a NAS. Even in Mountain Lion, the simple task of logging in my NAS with a different username and password and making aliases to shares on the NAS didn’t work correctly. Sometimes I can click on one of the aliases and it opens the share correctly, but usually it gives a stupid error message that probably means “I’m trying to connect as guest again even though you told me not to several times.”

Conclusion

In brief, the App Store made all of the difference in my full wipe and install of Mountain Lion. From now on I have new respect for the ease of installation provided by the App Store and I will avoid purchasing apps outside of the store wherever possible.

Carbon Copy Cloner performed exactly as promised, even guiding me through a few technical decisions that nobody should have to guess at.

It will probably be a few more weeks before I put away my backups, but I’m confident enough about this installation that I am ready to dump my old Time Machine backups and start Time Machine with a clean slate.

4 Responses to “Mountain Lion from Scratch—Not as difficult as I thought it would be”

  1. Jay writes:

    Thanks for this. I’ve been thinking about doing the same thing and your info has been invaluable.

  2. Henk Poley writes:

    You can download the printer drivers per brand from Apple. For example for HP: http://support.apple.com/kb/DL907

  3. mattoo writes:

    a bunch of thanks for this very valuable and detailed post !!

    I’m seriously thinking of re-installation my Mountain Lion from scratch since my (also) aging iMac is getting slower and slower, and your post covers all aspects of the job, so thanks a lot.

    I confirm that NAS connection is a real pain on Mac (dunno why) and furthermore tends to change with each OSX release :/ Found a little tweak that was helpfull, gotta remember the name before I reinstall, then I’ll post it there.

    The only thing I’d loved to find additionaly in your post is “does your aging iMac now work faster” ? I know you reinstalled for crash reasons, not performences, but still, did it make if run a little faster ?

    Thanks anyway for this post !

  4. Mr. Dana Leonard writes:

    Hi Tad. Thanks for the great site.

    In the article above, you state that “the Abbyy FineReader folks have finally fixed their ScanSnap app to support queueing without my script.” I’m sorry to bother you, but can you explain? I have FR that came with my ScanSnap S1500M as well as the full version of FineReader Express 8.3″ and despite repeated searches and attempts, I cannot figure out how to queue scans for conversion.

    Thanks in advance for your help!

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